Don’t expect Jimmy Kimmel and Jay Leno to exchange Valentines this year. In a new interview with Playboy, Kimmel once again lays into his fellow late-night talk show host, acknowledging that the “Tonight Show” star is “not just a smart politician but also a smart guy,” but explaining why he’s not shy about slamming him. “I always feel bad if I hurt anybody’s feelings, but I don’t believe Jay Leno has actual feelings, and he doesn’t seem to be that worried about other people’s feelings,” says Kimmel.

Back in 2010, Kimmel did an entire broadcast while imitating Leno — complete with prosthetics and a wig. “I can do a pretty good Leno imitation,” says Kimmel. “It was a lot of fun to be him — also much easier, particularly in constructing ‘his’ monologue for that night.”

Shortly thereafter, Kimmel appeared on Leno’s ill-fated 10 p.m. show, where he infamously mocked the host to his face during a satellite interview that Kimmel kept bringing back to Leno’s controversial replacement of Conan O’Brien as “Tonight Show” host. Kimmel recalls, “That was thrilling — it really was — and also kind of dangerous, because I realized he wanted to communicate to America that it was all just a friendly joke. That was the perception Leno clearly wanted out there.” “The more I thought about it the madder it made me. I didn’t want him to just get away scot-free with what was happening all over again,” explains Kimmel.

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